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Methodical history taking may help in timely diagnosis of spontaneous intracranial hypotension. Orthostatic headache (OH) is a key symptom of spontaneous intracranial hypotension (SIH). However, there is no optimal history taking for OH. A 35-year-old man complained of headache that prevented him from performing routine physical activities, which was relieved on lying down. We initially considered migraine as the most likely diagnosis. However, detailed history taking revealed that his headache worsened on standing, and he was finally diagnosed with SIH. Headache relief on lying down is not a specific indicator of OH associated with SIH. Thus, with regard to headache history taking, we suggest it important to confirm headache aggravation on standing.